


Pretty in Pink

by SupernaturalWaffle



Category: Supernatural
Genre: Age Play, BDSM, Bottom Sam Winchester, Crossdressing, Daddy Kink, Feminization, John Winchester Is Not An Asshole, M/M, Multi, Murder, Orphan Sam Winchester, Panties, Sam is a killer, Sam is a small twink, Sibling Incest, Slutty Sam Winchester, Spanking, Top Dean Winchester, Wincest - Freeform, tiny cock, unknowing incest
Language: English
Status: In-Progress
Published: 2016-06-09
Updated: 2016-06-09
Packaged: 2018-07-14 01:03:00
Rating: Mature
Warnings: Graphic Depictions Of Violence, No Archive Warnings Apply, Underage
Chapters: 6
Words: 2,474
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7145714
Author URL: https://archiveofourown.org/users/SupernaturalWaffle/pseuds/SupernaturalWaffle
Summary: <blockquote class="userstuff">
              <p>After giving Sam away for his own safety after Mary's death, fifteen years later Dean meets up with his brother, but Dean doesn't know that's his brother yet, or what he's done.</p>
            </blockquote>





	1. Goodbye, Baby

"Take your brother outside as fast as you can!", the man holding a baby said to the four year old, panicked, "Go, Dean, now!" Handing the baby to the child, watching him run, soon following.

\---

"B-but, dad! Don't make Sammy go! H-he can't! He can't!", Dean sobbed, not wanting his baby brother to be sent away, trying to take the baby away from his father, but John, who was also crying softly, looked at him.

"Dean, I'm sorry, I just-...Sam will be safer with someone else, okay?", looking at his son with sad eyes, trying to get him to understand. "You want Sammy safe, right?"

Dean, who rubbed his wet eyes, bloodshot from all the crying, nods ,"y-yeah.."

John touched his cheek sadly, "sometimes, to protect the ones we love, we have to let them go..", he softly said to his son, "I know it sucks, really bad, but it's to keep Sam safe."

 

"Can- can I see Sammy...before he goes...?"

John nearly sobbed at the request, the sad heartbreaking innocence in his son's voice. His mother lost in the fire, and now he was taking away his brother to keep him safe. He nodded, "of course.." Lowering Sam for Dean to see, the baby cooed, looked at his brother's green eyes as if to remember it forever. His little hand reached up and touched the lining of Dean's jaw. 

"It'll be o-okay, Sammy...", Dean whispered to the infant, more tears slid down his cheek, "we- we need to keep you safe, and that means you have to go away...", the child voice broke a little, and because he could see the sadness on his brother's face, the baby began to cry. "Sh, sh sh sh, it's-it's okay, Sammy, don't cry. Please." 

"Dean, would you like to hold him while I go pack what stuff we have left of his?", John asked, and Dean nodded, knowing this is the last time he get to see his baby brother.

\---

On the ride to the orphanage, Sam cried, and Dean sang 'Hey Jude' to him. The same song his mother did, and it calmed the small child. Dean snuck a necklace onto the baby, tucking it under the onesie he was wearing, "so you don't forget about me.", he whispered to the now sleeping child. The necklace had a little rectangular pink crystal rock on it, a Rose Quartz, dulled down so he couldn't stab himself by accident. 

He held his little brother, walking in with his father, Dean refused to let him go. A woman walked up to him, Dean felt tears fill his eyes when he saw her, she squatted down, asking, "can you hand me him, little buddy?"

Dean lost it in sobs, shaking as the four year old cried, "I'm sorry, Sammy...", he said to the sleeping child, who was beginning to awaken. "You can't take Sammy, he-he's mine." 

John squatted down and whispered, "Dean, you gotta let him go, this is why I wanted you to stay home...", he glanced at the woman, "I'm so sorry, he wouldn't stop screaming till I took him with me." 

She shook her head, "it's alright, not the first time this has happened." 

Dean cried, finally handing her Sam, "I'm sorry, Sammy, I'm sorry." 

The baby had awoken in the woman's arms, he looked into his older brother's eyes, the woman walked away with the baby's things, and you could ask Dean a thousand times, and he would tell you this no matter what, that baby whispered his first word when he was taken away, and he said "Dee.."


	2. The Biggest Slut is a Virgin

It's been fifteen years since the child Sam Winchester was orphaned, heels click as the wearer walks down the side walk, the hazel eyed boy looking around the dark sky, stopping in front of a bar to reapply his lip gloss and check his skirt isn't too high up. He heads to the back of the bar and grunts as he sneaks in the window.

Walking out of the bathroom he managed in, he walks to the bar, sitting on a stool, and he waits.... Playing that innocent look, like he's not dressed like a total slut. 

After a while, the bar tender walks down and sets down a margarita, Sam glances up and he says, "from the gentleman over there." Pointing over to this older man, probably in his mid-forties. 

Sam smiles, perfect, looks like a drunk looking for a good time, he takes his drink and walks over. "Thanks," he says in a soft voice, taking a sip.

The man smiles, the dirty geezer, puts his hand on Sam's soft thigh that still has some baby fat on it, "well, couldn't let a pretty little thing like you go thirsty." 

Sam glances down at his hand, biting his lip, glancing up, "well, then I guess I owe you one." Smiling as he takes another drink. Sam knows how he looks, not hit his growth spurt so he's short, his hair long enough to touch his shoulders, and soft smooth hairless skin. All that in a little short skirt, his plan was perfect for getting someone to want him. 

The man smirks, "we can work something out." Putting his hand on Sam's cheek, his thumb touching his plush glossed lips.

"Yeah, we can.", Sam practically whispers, taking the thumb in his mouth and sucking on it softly.

\---

After a night of flirting and dirty talk, even Sam flashing the man a peek of his panties, he was walking the man to his house, this abandoned building he found, humming as he closed the door and locked it behind them. 

"So, what'd you say your name was again?"

"Sam." 

He smiles, "Sam, simple, cute. I'm Henry, isn't this a little rushed, delicate flower?"

Oh, barf, ew. "What? You don't want to be the first one in my virgin ass?", Shaking his hips teasingly, because he's never slept with anyone, so he's not lying.

"Oh, baby, trust me, not what I'm saying at all." He purred.

Sam looks at him, "I feel like we've talked about me all night, what about you? Any...family? Friends?"

He shook his head, "new town, fresh start."

A smirk grew on the glossed lips, "perfect." 

The man smiled at Sam, ignoring the comment, pointing at the Rose Quartz necklace, "pretty little necklace."

Sam smiles and walks closer, "Isn't it?" Pecking his lips, his hand slides in his bag and he grabs a knife from it, he steps back quickly and slits the man's throat, closing his eyes as blood gets on his face. Sam spit a bit of blood out, "God, you where too easy. Usually I have to blow someone first.", he murmurs, rolling his eyes in a bit of disappointment at how simple and non-challenging this man was. He sighs and looks at the body that now lays on the floor.

Sam hums as he goes to shower, on to the next town.


	3. Those Damn Eyes

Sam sighs, holding his thumb up with his bag in his hand, walking down the side of an empty road, waiting for someone to stop for him. After about twenty minutes of walking, one did. A truck, the driver looking about fifty. His hair grey, a nice beard on his face, and deep green eyes. "Need a ride, cute lil thing?", obviously from the south side of North America. 

"That would be great," Sam replies, hopping into the car. When he caught sight of the eyes, it felt like some sort of sign. Like an alarm going off in his head, but only about his eyes. 

"Well, where's a doll like you headin'?", putting his hand on Sam's thigh as Sam closed the car door and buckled up. 

Sam looks at the hand, "anywhere would be awesome." Looking back up, but he couldn't look at the eyes. They drove him crazy. 

The older man chuckles and nods, "anywhere, alright, let's go anywhere." 

\---

Those few hours of driving felt painfully long to Sam, especially with the man obviously flirting. Though the wedding ring on his finger suggested he was a dirty unfaithful creep, just Sam's type. Not to date, obviously. His name was George, and there's a picture of an young adult woman on the window, not his wife, must be the daughter. She was holding a baby, he's a grandfather, a dirty grandpa. Heh, suck it, Johnny Knoxville. 

When they where far enough to be in a different state, Sam smiles over, "Hey, George?" 

"Hm?"

Using this innocent, yet slutty sweet voice, "you wanna play a game?"

George smirks a bit, nodding, "what kind of game?"

"Well first, I need you to stop the car."

And he did, looking over at Sam, Sam undid his seat belt. Grabbing a scarf from his bag, he can't do this with green eyes on him. "Now, I'm gonna put this over your eyes." 

The man chuckles, "You some kind of freaky," he said as Sam wrapped the scarf around his eyes, blind folding him. 

Sam smiles, pleased, he moved and sat on the man's lap, "now I," kissing on his neck, "Get to do whatever I want to you." He whispered, kissing all around his neck. Grabbing out hand cuffs. 

"Go ahead, little one.", the man said, Sam sliding both the man's hands behind his back and cuffing then. 

Kissing down his chest, making his way to his belt, the man let out a breathy chuckle as Sam undoes it. Pulling out the hairy prick's prick. Sam wrinkles his noes, but sounds seductive though, "So, do you love your wife?"

The man was obviously surprised by the question, "wha'?"

"Well," stroking the man, "you have a wedding ring on. How would your wife, daughter, and grandchild feel about you being so unfaithful?" 

He scoffs, "I don't give a rats ass." 

Sam glares, grabbing out hedge clippers, putting the blades on either side of the cock, "Dirty old creep." Then he chops, off his manhood goes. 

The man starts screaming, "what the fuck?! You little bitch! I'll kill ya'!" Squirming around the handcuffs.

Sam rolls his eyes, grabbing the cut off cock, "Eat a dick." And stuffs the cock down the man's throat. The man gags, trying to get the cock out of his throat. Sam chuckles, grabbing the hedge clippers, and stabbing him in the chest with the blade, humming softly as he pushed the man to the passengers seat, "Just sleep, I'll drive the rest of the way." Smiling as he starts the car with the lifeless body beside him, and drives away.


	4. Chapter 4

**Notes for the Chapter:**

> Hey, sorry, I've had major writers block

Sam sighs, looking at the truck as it sinks in the river he's leaving it in after driving for hours with the dead body, once it's all the way down and nothing pops back up, he walks away with his bag of things. Walking the rest of the way, an hour of walking before he makes his way into some small town, feeling dirty and sweaty, he needs a place to sleep and something to eat. He walked around, finding some restaurant, a small little diner, and walked in the bathroom, cleaning himself off.

He walks back out with his make up reapplied, a hot pink tank top, a pastel pink see-through long sleeve over shirt, a pink rose flower crown, his necklace showing, and white short shorts. 

Walking over to a table, a waiter walks over and Sam looks at him, "hi." Smiling all innocent, "can I get, uh," looking at the menu, "a Asian salad please? Also, an ice tea?"

The waiter stars at him adoringly, nodding "is that all?" 

Sam smiles as he nods. 

Two men walk in, but Sam doesn't look at them, he goes to get his bag to grab his brush, realizing he left it in the bathroom, his eyes widen and he goes to get up, but his body is so tired, his legs give out and he starts to fall, but he feels a body grab him, holding him up, he looks up to see green eyes staring him down, the light brown, or maybe dirty blond, hair on his head, freckles all over the concerned face, and the deep voice asking:

"Woah, you okay?"


	5. Stubborn, what an understatement.

**Notes for the Chapter:**

> IM SO SORRY FOR HOW IVE BEEN SLACKING ON WRITING. IVE BEEN BUSY PLEASE DONT HATE ME.

Sam's breath hitched as he looked up at the man, blushing with embarrassment, "I-I'm...I'm fine...just need to get my bag."

But the man shook his head, "No, no, alright? You look like you're about to pass out. Sit. I'll get it." 

Sam huffed, stubborn, "No, I don't need help." 

The boy's brows frown, "Fine. Go get it then." Smirking a bit cocky. 

Sam huffed, "Fine, I will." 

"Cool, do it." 

"Fine." 

"Fine."

Sam pauses, just being held by the man's arms, an older gentleman with dark hair and brown eyes glancing at them, "Dean, leave the girl alone." 

He looked over at the older man, "I'm just messing around, dad." 

Sam snickers, "Aw, you playing with daddy?" 

Dean glances at Sam, letting out a huff, "well, aren't you a mean girl." 

Sam smirks up at Dean, "What? You find the mean girls hot?"

He chuckles, "More of a fun challenge, cutie." 

Sam makes an innocent face, "So you think I'm a cute girl?" 

Dean smiles, "Anyone would, doll." 

Sam giggles, "Well I'm a dude, with a fully functional penis," standing up, Dean's jaw dropped and John laughs so hard he's pounding the table, "See ya, stud." Smirking as he walked away


	6. Fake News

**Notes for the Chapter:**

> IM NOT DEAD I JUST LOST MY PASSWORD

Sam sigh as he walks, making his way into the bathroom and grabbing his bag, and making his way back to his seat. He could feel those piercing green eyes on him, but he pretended not to. He smiled at the waitress as she brought him his food, "Thank you,"

He began to eat, the news coming on to them talking about a series of men who have gone missing. When Sam heard them say they have no suspects, and they can't find how they are all connected besides that they're married men, he smirked. He then noticed the two men paying very close attention, a little too much to be comforted with. What? Is it their job, or something?

 

He listened closely hearing them say something about the men possibly being unfaithful, and something about a...woman in white? Oh well, at least it's not me. The older man denied the idea, claiming they stay at one certain area. What the hell?

He finished his meal and walked over to the younger of the two, "you know where the nearest motel is?"

He clears his throat and nods, "uh, yeah, go down the block and take a left, it's three blocks down from there..." 

Sam flashes a smile and nods, "thanks..", he raises a brow as his eyes go wide, looking down at the dulled down, pretty pink, Rose Quartz necklace sitting there on his chest..

**Author's Note:**

> This is my first posted story ever please don't kill me


End file.
